Amido-amide derivatives of oxalic acid and processes of preparing the same



Patented Sept. 2, 1952 AMIDO-AMIDE DERIVATIVES OF OXALIC ACID AND PROCESSES OF PREPARING- THE SAME- Herman B. Goldstein, Cranston, and Stanley T. Clary, Coventry, R. I., assignors to Sun Chemical Corporation, Long Island corporation of Delaware City, N. Y., a

No Drawing. Application ctober 5, 19 49,

Serial No. 119,755

The present invention relates to new organic compounds which-are valuable as assistants in the treatment and-finishing of textile materials.

One object of the present invention is to providenew Waterv dispersible organic-compounds useful for the treatment of textile materials which, upon such treatment, impart a highly improved hand and enhanced texture thereto.

Another object of the present invention is to provide new water dispersible organic compounds which are substantive to textile materials and which are highly resistant to ordinary laundering and dry cleaning methods after application thereto, thereby imparting arelatively permanent finish to such treated textiles.

Another object of the present invention is to provide new water dispersible textile finishing agents which do not cause discoloration nor yellowin of textile materials treated therewith, which are effective over long periods of time and under al1 the-ordinary operations and conditions to which such textiles are subject, and which do not effect any color change in the shadeof dyed fabrics, nor which deleteriously affect the light fastness of dyestuffs.

, Other objects of the present invention will be apparent from the following description and appended claims; I

It has been found that the above objects may be accomplished and that organic compounds having the properties and characteristics described therein may be prepared by reacting a high molecular Weight aliphatic carboxylic acid, or derivatives thereof, such as the esters or halides thereof, with a polyamine to form an amido amine of such acid, and thereafter reacting the resultant amido amine with a dibasic acid,or a derivative thereof, such astheanhydride, esters or acylhalides thereof, in such manner that a disubstituted derivative of the dibasic acid is formed. Y v

The organic compounds formed according to the process of the present invention may be considered to be disubstituted amido-amide derivatives of dibasic acids. Similarly, these products may also be considered to be acyl amides of a dibasic'acid and high molecular weight aliphatic carboxylic acids. 7 v

. The high molecular weight aliphatic carboxylic acids employed in preparing the above mentioned amido amines are those containing at least six carbon atoms in the aliphatic chain, as for example-caproic acid, caprylic acid and capric acid,

and preierably those containing atleast twelve carbon atoms in the molecule. Among those acids which are preferred for use in the present invention are;the;higher saturated fatty acids aslauric acid, myristic acid, palmytic acid,

7 11 Claims. (Cl. 260-4045) stearic acid, animal and vegetable oil saturated fatty acid. compositions such as coconut fatty acids, and hydrogenated fatty acid compositions, such as from hydrogenated fish oils, hydrogenated cotton seed oil, hydrogenated soy bean oil and hydrogenated peanut oil. The higher unsaturated fatty acids as. for example, oleic acid, palmitoleic acid, linoleic acid, linolenic acid and eleostearic acid, may also be employed in preparing the compounds of the present invention.

However, theme of such acids is not preferred since the end product, that is, the softener compound, displays a tendency toward slight discolorationdue to'the unsaturation in the finished product. f

'The polyamines which are reacted with the above mentioned acids to provide the amido amines which may be subsequently reacted with a dibasic acid to provide the new organic 'compounds of the invention,: comprisethose polyanii'nes containing at least two amino groups of the primary or'of the secondary type and which may contain one or more aliphatic residues in the molecule. Examples ofsuch polyamines include the diamines such as ethylene diamine, trimethylene diamine, tetramethylene diamine, pentamethylene diamine, and hexamethylene diamine; the polyethylene polyamines such as diethylene triamine', triethylene tetramine, tetraethylene pentafn'ine, "etc.; substituted diamines such as ethyl ethylene diamine, hydroxyethyl ethylene diamine, N-N'dihydroxyethyl ethylene diamine, N-ethyl N '-aminoethyl ethylene diamine; and such other polyamines'as diaminoethyl ether and diaminoethyl thio'ether.

' Polyamines of the type exemplified above may be reacted with any of the previously mentioned aliphatic carboxylic acids to provide an amido amine containing at least one free primary or at least one' free. secondary amino group which is available for further reaction under proper conditionswiththecarboxyl groups of a dibasic acid, thus forming a diamide derivative of the said dibasic acid.v 1

Among the variousfldibasic acids which, when treatedwithj'the amido amines under the conditions hereinafter-set forth, will furnish the organic compoundsfo'f thepresent invention, may be 1isted,. the, aliphatic dicarboxylic acids as oxalic acid, 'i'nalonicfacidgsuccinic acid, glutaric acid,

adipic acid,,pimelic acid, suberic acid and sebacic acid; the unsaturated aliphatic dicarboxylic acids such as maleic and ,fumaric acids, and". cyclic aliphatictdicarboxylic acids such as 1-4 cyclohexane dic'arb'oxylic acid, and aromatic and alkyl' aromatic 'dicarboxylieacids such as phthalic acid,".isophthalicyacid, homophthalic acid and uvitic acid. Other dibasic acids, substituted or mentioned dibasic acids may also be employed in carrying out the invention l,

The compounds obtained in accordance with the procedures hereinafter outlined and with the materials above set forth may be represented by the following general formula:

that a ate ism ma i and Re represent an aliphatic chain containing nve tr mor; carbon atoms. Furthermore, R1 and Rrjiha'y be identical .0; they may be different, depen'diiig 'upfon whether the radicals represented by R1 and, Rf: are derived from the same acid or from different acids. R2, R3, R5 and Re may represent hydrogen, a

allryl r'adical, or a loWer hydroxyalkyl radical, the various substitu'ents corresponding to the terminal substituent'sfoccurring in the par- V "endear. may. further represent an 'acyl residue of anfaliphatic carboxylic acid. The particulariconi'p'ounds inwhi'ch R3 and R5 have such representation s eamer eiiample, in an amide aminein whichthe polya'mihe 'has been so reacted with ahjalipha'tic 'c'arb'oxylic acid that both terminalfainino gr u'ps contain an acyl radical and'in which at least'onelof the acyl substituted amino groups contains a free hydrogen atom.

. Depending upon the particular polyamine employed in preparingfthe amido amine, G in the above' forinula maybe a secondary amino group, a simple loweralkyl or lower alkylol substituted amino'g'rougoxy'gen'or sulfur.

The letters a, b,'c, d, e and frepresent integers, a andc representing integersfromfl to 6; and b, d, eand 1 representing integers from 1 to 6. I

That portion of the above I general formula represented by X is a dicarbo'xylic acid residue in which R4 may represent anjaliphatic group, a

cyclo aliphatic group, an aromatic group or an alkyl aromatic group. Rimay also represent any of the said groups substituted within theirstructure by halogen, oxygen, and sulfur atoms, or by amino, ester, hydroxyl, and ether groups, or any of the said groups in which the carbon linkage is interrupted by halogen, Oxy en or sulfur atoms, orby'an amino, ester, hydroxyl, or ether group. 7 The compounds represented by the above general formula and the methods of preparing the same are described and claimedin our copending patent application, Docket 33 4, filed'on even date herewith. v p V 7 As has been jsetfor'th above, X in the general formula represents a dicarboxylic acid residue. The linkage between, the two carbonyl groups contained in the said dicarboxylic group need not represehtedby' Ri'but'may bea simple linkage such as is had in oxalic acid. This @ype of linkageis obtained when oxalic acid wherein X represents the \u c itexyne residue of oxalic acid and wherein allthe remainifigsubsti tuents of the compound correspond to those of the preceding general formula as designated by the corresponding symbols therefor.

The organic compo'unds'of the present invention, as represented by the above illustrative for. mula sare'preparediby reacting between approximately one mol a tends of an aliphatic'ear boxylic acid containing at least six carbon atoms in the aliphatic ch'ain With approximate y the mot r a polyarhi'neof the "type vicusly d8- scribed at a temperature'bettvee'n 'appzftfiiiinately 150 e u substantially complete reaction is obtained, thereafter adding approximately e an bidr a "ditasic acid a a fur-- i sr,... aiee im at. e a e between apprintimately wil -2110' "(3., depending upon the particular reiaction- Y/ 'i trials employed, until Vsubstantiallyjcornpletereactien secure as evidenced by ith runway 15w 'afnine value of the'reaction p ecast. niprouucts obtained in this manner, when 6001, are enemny an colored, wax-like, materials which [are "at least partially dispersible in hotwater. murder to insure complete aqueous di s'persio'n bf unproducts of the present invention, it isjaener n preferable to add a solubilizilflg ag" t thereto, such asga lower amend, or ajpeptizing'a g'entjsuch as an'alkali, o nicacid, asoapfetc. I

Where the do famine which isto be reacted with a dibasic acid contains more than one amino group in the molecular chain, more fthan one dicarboxylic acid residue may be introduced into the structure of the compound p'y increasing moncunr, quantity of the diba slc'achllh proportion to themoleclilafr amount'of the amide amine tobe reacted. T-hu sly, "merging symbols a and c in the-above illustrative formulaefare at least one and Where G represents a'sebonq ry amino group, asecond dicarboxyl'ic acid residue may be rea mitte into 't-h e structure of "the compound, linking p; 1ast;two ofthe ami o groups represented by G. One example of such a compound, and afinethodwherebythe same-1s be worked u into a pdnbentratedfiater'sbiume softener pastafby eatirientbfthe same with low molecular pr amp acids such as refinancetic, propionic, and lactic acids. Similarly, water soluble softener pa te which are particularly suitable for application 'to textile "materials may also be prepared by treating the organic compounds' obtained according to the-processes of the present invention with caustic potash, cat'stie soda, and similar alkaline materials. Such pastes are usually prepared by heating the compounds to a temperature at which the said compounds are liquid and then adding the said low molecular'acid or the alkaline material, as the case may be, plus an amount of water sufficient quantities of all materials employed therein are set forth in parts by weight.

I Example 1 276 parts of triple pressed stearic acid and 104parts of hydroxyethyl ethylene diamine are heated together at 180 C. while removing the water which is formed by their interaction, until the acid value of the reaction mixture is reduced to approximately 5 mgm. KOH per gram. This reaction yields approximately 362 parts of a material which consists predominantly of a mixture of materials corresponding to the two formulas The above reaction mixture is kept at 180 C. while 6'7 parts of diglycolic acid are slowly added thereto. As the diglycolic acid is added, a reaction occurs with the evolution of water. After all the diglycolic acid has been added, the temperature of the reaction mixture is raised to approximately 190 C. and kept at that point until further reaction ceases. There is thus obtained approximately 400 parts of material which, at room temperature, is a dark tan, brittle, waxlike material having .an acid value of approximately30 mgm. KOH per gram and anamine value of approximately 25 mgm. KOH per'gram.

.The reaction product thus obtained comprises 'whicl'i isdispersible in-hot water. tiles are'padded through a textile treating bath ties.

'6 In-preparing-a softener paste suitable for the treatment'of'textiles, 35-parts of the reaction product-obtained above are heated with 3 parts of 45% caustic potash and 62 parts of water, and themixture stirred until-uniform. There is obtained,-when cool,-alight tan colored, soft paste When texcontaining1% of thispast'e, the fabric is made 'soft to the touch and has excellent draping quali- This effect issubstantially unaffected by washing or dry "cleaning. When this product is applied to dyed fabrics it has'no effect upon the color shadeof the fabric, nor does it produce any deleterious effect on the light-fastness of the dyestuffs in the fabric.

Example 2 To 362 parts of the reaction product of stearic acid and hydroxyethyl ethylene diamine, as obtained in Example 1, there are added 74 parts of phthalic anhydride while maintaining the temperature of the mixture at approximately C. After all the phthalic anhydride has been added, the temperature of the reaction mixture is gradually raised to C. and held at that point until the reaction ceases. There are obtained approximately 420 parts of a material which. solidifies to a light tan colored wax-like material on cooling. The material thus obtained corresponds predominantly to the following formula:

.KOHper gram.

- Depending upon the .eduipment used and other factors; influencing-;the reaction, it is sometimes necessary to .add'na small additional amount of .phthalicanhydride: to the reaction mixture to compensate foriphthalicianhydride lost by sublimation, thus insuring substantial completion of the reaction 'I'his;'isllikewisetrue when using other dicarboxylicya'cids or. derivatives thereof which tend. .to distill, sublime or decompose at the reaction. temperatureslused. in. the present processes. I

- The'reactioni product obtained above may be worked up into a water dispersible paste by stirring 25 parts of the said reaction product with 4 parts of acetic acid and '71 parts of water, the temperature while-mixing being sufiiciently high to cause the reaction product to melt. When cool, the resultant paste is light tan colored and forms opalescent solutions when dispersed in hot water. Cotton fabrics or other textile materials upon immersion in a 1% aqueous solution of this paste, and subsequently dried, have a much softer hand than similar untreated fabrics.

Emample 3 the mixture slowly heated t'o'180 C. while passin'g nitrogen 'therethrough. When the evolution of water ceases, and the acid value of the reaction product has dropped to approximately mgm. KOI-Ipergram, there are then slowly added 118 parts of succinic acid while maintaining the temperature of the reaction mixture at approximately 185-l90 C. whilecontinuing the passage of nitrogen through the mixture. After all the succinic acid has "been added, the temperature is then further raised to 200 210" C., and held in that range until the reaction is substantially complete. Upon cooling. ;a brown wax-like material is obtained which it is believed 'comprises in part a mixture of materials corresponding to the following formulas:

5H C11H35C-4C2H4 N-CgH l ,L- -03 (Hi "ASH: "(EH2 2:0 =0 C liHiiFC LN-G l r C l| H and 0 mi n t To prepare a softener paste, 20 parts of the product obtained as described above is heated with 75 parts of water and 5 parts of 47% caustic soda, and the mixture stirred until homoeneous. When further diluted with water to a concentration of approximately 1--l0% and applied to textiles, this product imparts a soft feel to the cloth which is veryfast to washing and dry cleaning. Example *4,

225 parts of coconut fatty acids are lieaited with 148 parts for vNZN dihydroxyethyl ethylene diamine at id -:0 until theacidvalue'oftheira action mixture drops to approximately '5 imgms. KOHiper gram :or less.

wherein R. represents the aliphatic residue of coconut -fatty acids.

'-A textile softener :paste may he prepared *by -75 stirring 20 parts of the react-ionproduct of Example '4 in parts of a 3% tallow soap solution. Textile materials, when treated with an aqueous textile treating loath containing a 0.5% solution of the softener paste, acquire a pleasinglys oft'feel. This effect is substantially unaffected by washing or dry cleaning.

Example 5 g 284 parts of pure stearic acid is reacted with "104 parts of hydroxyethyl ethylene diamine at C. until the acid value of the reactionprodfuct-falls to less than 5 mgms. KQH per gram. The temperature of the reaction mixture is held at 170 C, while 50 grams of anhydrous oxalic acid areadded in small portions. Vigorous agitation is maintained duringthe addition of oxalic acid in order to break the foam which forms. When addition of oxalic acid has been completed, the temperature of the reaction mixture is raised to 'G. and kept at that 'point until the reaction is substantially completed, as indicated by an amine value less than approximately 30 mgms. KOH per gram. The reaction product thus obtained is a light tan'colored wax-filmma- "teria'l having a melting point of approximately a n concentrated softener ipaste, using the reactionproduct of Example 5, may be prepared as renews.

35 parts of the said reaction product, 2 parts caustic potash, -.02 part of-an anti-foam agent, and 52.98 parts water are heated to 80" C. and stirred until a uniform composition is obtained. 10 parts of 99% isopropanol are then stirred in, and the mixture is allowed to cool. The resultant softener paste has a light tan color and forms opalescent solutions when dispersed in warm water. When a textile treating bath is prepared with approximately 15 grams of the softener paste per liter of water, and textiles are treated therewith, a very soft, pleasing finish is imparted to the goods which is not noticeably affected by washing or dry cleaning. Moreover, the finish does not yellow or discolor white goods nor does it deleteriously affect the light fastness nor the color shade of 'dyedfabrics.

predominantly to the Example 6 To 3'70 parts of the pie-condensate prepared by the reaction of stearic acid and hydroxyethyl ethylene diamine as described in Example 5, there are slowly added 86 parts of diethyl fumurate while maintaining the temperature of the mixture at "150 C. When all of the diethyl fumurate has been "added, the temperature of the mixture is. slowlyraised to. 190 C., and is held at that point- ;until substantially complete reaction has been. obtained. When the reaction product has cooled; there is obtained approximately 410 parts vof a dark brown, hard, waxlike material, corresponding for the most part to the following formula: I

A concentrated softener paste 'may be prepared by heating 25 parts of the reaction product obtained above with parts of triethanolamine and 70 parts of water, and stirring the mixture until uniform. When'this' paste is further diluted with water to a concentration of approximately 1-10% and appliedto textiles, particularly. cellulos'ic textiles, a marked softening actionion the fabricis obtained.

ma e.

290. parts .015 hydrogenated fish oil fatty acids are heated to 1501C. and approximately 90 parts of 70%1ethylene diamine=are gradually introduced below the surface of. the molten fatty acids. After all -the amine has been added the mixture is slowly heated to 170 C.;and kept at that point ,until the acid value-drops to approximately 10;;m ma KOH per gram 1 While main taining the temperature of the reaction'mixture.

in which R1 and R7 represent the aliphatic residues of hydrogenated fish oil fatty acids.

When the amine value" of the above reaction mixture drops to a minimum, the mixture is cooled to approximately 90 C. parts of 45% caustic potash are then added thereto, followed by 1500 parts of hot water: The mixture is stirred until uniform, and is then allowed to cool. There is obtained approximately 1900 parts of a light tan coloredpaste- When thispaste is further ,diluted'with Warm water andapplied to tex tiles, a soft'feeljis imparted to the textiles. This softening. effect is not materially aifected by dry cleaning orwashingf r Example 8 225 parts of coconut fatty acids and 116 parts of N,N'diethy1 ethylene diamine are heated together to a temperature of approximately 180 C., and the reaction mixture is maintained at that temperature until the acid value of the mixture drops to less than approximately 10 mgms. KOH per gram. To the resulting reaction product there are added, in small portions, 72 part of phthalic anhydride. Upon completion of the addition of the phthalic anhydride to the reaction mixture, the temperature of the reaction mixture is gradually raised to approximately 200 C. and maintained at that point until reaction issubstantially complete, as exidenced by a low amine value. Upon cooling to room temperature, a light, tan colored wax-like material is obtained.

In preparing a softener paste for'the treatment of textiles employing the reaction product secured above, the molten reaction product is cooled 0 a temperature of approximately C., and 40 parts of an aqueous 45% potassium hydroxide solution are added thereto. The mixture is stirred'until homogeneous and there are then added thereto 1100 parts of 'hot water; stirring being continued until the mixture is again homogeneous. The resultant softener paste may then be dissolved in water in predetermined amounts Example 9 288 parts of caprylic acid are heated to a temperatur of approximately C., and '74 parts of propylene diamine are gradually introduced thereto beneath the surface of the acid. The temperature of the mixture is then raised to approximately C. and maintained thereat until reaction is substantially complete, as evidenced by an acid value of less than approximately 10 mgms. KOH per gram. Depending upon the ,equipmen't' used and the conditions of the reaction when 'usingl a relatively volatile amine such as propylene diamine, it is often found that a satisfactorily low acid value cannot be obtained by the use of the theoretical amount of the. amine. In such case it is necessary to add an excess of' the amine" to compensate-for the amine lost by'vaporization. The reaction described above yields approximately 326 parts of a material which is substantially of the follow.

ingformula: v

often; no,

i'Th'e product thus obtained is dissolvedinapproximately500 parts .toluol andreacted therein With- 91.5 partshexanedioyl chloride at approximatelyl85 C. in the presence of a hydrogen chloride acceptor such as pyridine. At completion 'of the reaction,- the reaction mixture is quickly transferredintoboiling water andthe mixture is 'agitatedivig'orously. Thereafter the 1 Water is drawn offl'and the toluol removed under 11 material, corresponding predominantly to the formula The product thus obtained may be dispersed in aqueous solution with caustiq alkali, or acetic acid in such manner as has been set out hereinhefore to form a softener paste which provides improved drape to textile materials when applied thereto and which has no adverse effect on the light fastness properties of dyestuiis.

Example 276 parts of triple pressed stearic acid are reacted with 104 parts of B,B'-diaminoethyl ether at 170 C. until the acid value of the reaction mixture drops to less than approximately 5 mgms. KOH per gram. The temperature of the reaction mixture is then raised to approximately 190 C.; then 59 parts of tartaric acid are added thereto in small portions. The temperature of the reaction mixture is maintained at this point until a substantially complete reaction has been obtained as indicated by the relatively low amine value of the reaction product. The reaction product consists predominantly of a compound having the formula A concentrated textile softener paste may be prepared by heating parts of the product of Example 10 with 75 parts of water and about 5 parts of 47% caustic soda, and stirring the mixture until homogeneous.

The hand and texture of textile materials treated with the compounds of the present invention are not only greatly improved over those of untreatedfabrics, but the particular proper ties imparted to the fabric by the use of such compounds may be varied according to the specific compounds employed. For example, those compounds, in which the aliphatic chain portion represented by R1 and R1 in the illustrated general formulas is one containing less than 18 carbon atoms, impart exceptional softening effects to the fabric, while substantial bodying of the fabric with less softening effect is had when the compound employed in the treating bath is one in which the said aliphatic radicals consist of chains containing more than 18 carbon atoms. The particularly desirable properties imparted to the textile fabrics by the treatment thereof with the compounds of the present invention are substantially permanent due to the substantivity of these compounds toward textile materials, and particularly towards cellulosic fabrics. Due to the absenceoi primary amino groups in the compounds of the present invention, there is little danger of yellowing or discoloration of the fabric under conditions of heat, humidity; or long storage of the goods. As has been pointed out, the finishing agents of the present invention have no efiect upon the color shades of dyed'fabrics and do not adversely aiiect the light fastness of dyestuffs commonly used in coloring textile materials.

While the above products and processes of making the same constitute preferred embodiments of the present invention, changes may be made therein without departing from the scope of the invention as defined in the appended claims.

What is claimed is:

1. A chemical compound corresponding to the formula where R1 and R7 are aliphatic chains containing at least 5 carbon atoms; R: and Re represent a radical of the group consisting of hydrogen, a lower alkyl radical, and a lower hydroxyalkyl radical; R3 and R5 represent a radical of the group consisting of hydrogen, a lower alkyl radical, a lower hydroxyalkyl radical, and an acyl group containing at least 6 carbon'atoms; G rep resents a radical of the group consisting of an amino group, a lower alkyl substituted amino group, a lower alkylol substituted amino group, oxygen and sulfur; a and c represent integers from 0 to 6', and b, d, e and 1 represent integers from 1 to 6.

where R1 and R7 are aliphatic chains containing at least 5 carbon atoms; R: and Rs represent a radical of the group consisting of hydrogen, a lower alkyl radical, and a lower hydroxyalkyl radical; R3 and R5 represent a radical of the group consisting of hydrogen, a lower alky1radical, a lower hydroxyalkyl radical, and an acyl group containing at least 6 carbon atoms; and where b and (1 represent integers from 1 to 6.

3. A chemical compound corresponding to the formula where R1 and R7 are aliphatic chains containing at least 5 carbon atoms; R2 and Rs represent a radical of the group consisting of hydrogen, a lower alkyl'radical, and a lower hydroxyalkyl radical; R3 and R5 represent a radical of the group consisting of hydrogen, a, lower alkyl radical, a lower hydroxyalkyl radical, and an acyl group containing at least 6 carbon atoms; G represents a radical of the group consisting of an amino group, a lower alkyl substituted amino group, a lower alkylol substituted amino group, oxygen and sulfur; and where a and represent integers from 1 to 6.

4. A chemical compound corresponding to the formula where R1 and R1 are aliphatic chains containing at least 5 carbon atoms.

5. A chemical compound corresponding to the V formula where R; and R7 are aliphatic chains containing at least 5 carbon atoms.

6. A process for the preparation of a disubstituted amido amide of oxalic acid which comprises reacting the condensation product of an aliphatic carboxylic acid containing at leastfi carbon atoms and a polyamine, said condensation product containing at least one amino group which contains free hydrogen, with oxalic acid at a temperature between approximately 150- 210 C.

7. A process for the preparation of a disubstituted amido amide of oxalic acid which comprises reacting an aliphatic carboxylic acid containing at least 6 carbon atoms with a polyamine at a temperature of 150-180 C. to form a condensation product containing at least one amino group which contains free hydrogen, and thereafter reacting said condensation product with oxalic acid at a temperature between approximately 150-210 C.

8. A process for the preparation of a disubstituted amido amide of oxalic acid which comprises reacting the condensation product of an aliphatic carboxylic acid containing at least 6 carbonatoms and a polyamine, said condensation product having not more than one primary amino group, with oxalic acid at a temperature between approximately -210 C. to form a condensation product vfree of primary amino groups.

9. A process for the preparation of a disubstituted amido amide of oxalic acid which comprises reacting an aliphatic carboxylic acid containing at least 6 carbon atoms with a polyamine at a temperature of 150-180 C. to form a condensation product having not more than one primary amino group, and thereafter reacting said condensation product with oxalic acid at a temperature between approximately 150 210 C. to form a condensation product free of primary amino groups. i

10. A process for the preparation of a disub I stituted amido amide of oxalic acid which comprises reacting the condensation product of an.

aliphatic carboxylic acid containing at least 6 carbon atoms and a polyamine, said condensation. product having no primary amino groups and not more than one secondary amino group, with. oxalic acid at a temperature between approximately 150-210 C. to form a condensation product free of primary and secondary amino groups.

11. A process for the preparation of a disubstituted amido amide of oxalic acidwhich comprises reacting an'aliphatic carboxylic acid containing at least 6 carbon atoms with a polyamine at a temperature of 150-180 C. to form a condensation product having no free primary amino groups and not more than one secondary amino group, and thereafter reacting said condensation product with oxalic acid at a temperature between approximately 150-210 C. to form a condensa REFERENCES CITED The following references are of record in the file of this patent:

UNITED STATES PATENTS Name Date Robinson et al. Aug. 12, 1947 Number 

1. A CHEMICAL COMPOUND CORRESPONDING TO THE FORMULA 